Journal
CHEMCATCHEM
Volume 5, Issue 5, Pages 1192-1199Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201200723
Keywords
amination; amino acids; asymmetric synthesis; carbonyl compounds; sustainable chemistry
Categories
Funding
- ANR [ANR-07-BLAN-0269]
- Aix Marseille Universite
- CNRS
- Universidad del Valle (Cali, Colombia)
- COLCIENCIAS
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The first organocatalytic general, efficient and highly enantioselective -hydroxyamination reactions of -ketoamides with nitrosobenzene are described using a thiourea/tertiary amine bifunctional catalyst. Significantly, the products were obtained in high enantiomeric purity using a low catalyst loading, and in the context of sustainable development, the full reaction mixture, including solvent, catalyst and excess substrate, can be recycled without significant erosion in the efficiency and enantioselectivity of the reaction. The described catalytic transformations secure a practical synthetic access to stereodefined and conformationally constrained -amino acid derivatives exhibiting a quaternary chiral center at the position.
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